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Home / Phosphorus, Sulfur, and Silicon and the Related Elements, Volume 179, Number 1

AN UNEXPECTED CYCLIZATION DURING NUCLEOPHILIC ADDITION OF 5-MERCAPTOQUINOLINE TO PHENYLACETYLENE

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Reaction of 5-mercaptoquinoline with phenylacetylene (KOH, dioxane, 160–170°C, 1 h, autoclave) gives (along with the normal adduct Z-5-styrylthioquinoline) 3-phenylthiopyrano[4,3,2-d,e]quinoline, the product of a unique intramolecular nucleophilic substitution of hydrogen by carbanion at position 4 of the quinoline ring.

Keywords: 3-phenylthiopyrano[4,3,2-d,e]quinoline; 5-Mercaptoquinoline; Z-5-styrylthioquinoline; carbanion; nucleophilic addition; nucleophilic substitution; phenylacetylene

Document Type: Research Article

Affiliations: Russian Academy of Sciences, Siberian Branch Irkutsk, Russia

Publication date: 01 January 2004

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